M. Abaszadeh et al.
CH3), 0.81 (s, 3H, CH3). 13C NMR (100 MHz, DMSO-d6) d: 192.71 (C=O), 156.08,
153.27, 152.59, 137.96, 136.48, 132.71, 131.48, 113.35 (CN), 61.68 (C3), 55.63
(OCH3), 48.25 (CH2), 37.36 (CH2), 36.58 (CH), 32.69 (CMe2), 29.34 (CH3), 27.24
(CH3). Anal. calcd. for C19H21N3O2: C, 70.57; H, 6.55; N, 12.99 %. Found: C,
70.43; H, 6.48; N, 12.82 %.
2-amino-4-(4-bromophenyl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-
carbonitrile (4c)
Yellow crystals; IR (KBr, mmax,cm-1): 3,392, 3,328, 3,232 (NH2, NH), 2,192 (CN),
1
1,654 (C=O), 1,596 (C=C). H NMR (400 MHz, DMSO-d6) d: 8.93 (s, 1H, NH),
3
7.45 (d, 2H, JHH=4 Hz, CH–Ar), 7.08 (d, 2H,3JHH=4 Hz, CH–Ar), 5.82 (s, 2H,
2
NH2), 4.30 (s, 1H, CH), 2.42 (d,2JHH=8 Hz, CH), 2.31 (d, JHH=8 Hz, CH), 2.18
(d,2JHH=8 Hz, CH), 1.98 (d,2JHH=8 Hz, CH), 1.02 (s, 3H, CH3), 0.90 (s, 3H, CH3).
13C NMR (100 MHz, DMSO-d6) d: 191.89 (C=O), 155.88, 154.12, 136.70, 134.34,
132.19, 131.79, 128.86, 113.41 (CN), 60.61 (C3), 49.59 (CH2), 40.89 (CH2), 39.91
(CH), 33.53 (CMe2), 30.22 (CH3), 28.82 (CH3). Anal. calcd. for C18H18BrN3O: C,
58.08; H, 4.87; N, 11.29 %. Found: C, 57.91; H, 4.75; N, 11.05 %.
2-amino-7,7-dimethyl-5-oxo-1-phenyl-4-(p-tolyl)-1,4,5,6,7,8-hexahydroquinoline-3-
carbonitrile (4e)
Yellow crystals; IR (KBr, mmax,cm-1): 3,472, 3,344 (NH2), 2,176 (CN), 1,651
(C=O), 1,590 (C=C). 1H NMR (400 MHz, DMSO-d6) d: 7.63–7.12 (m, 9H, CH–Ar),
5.31 (s, 2H, NH2), 4.42 (s, 1H, CH), 2.21 (d, 2JHH=4 Hz, CH), 2.17 (d, 2JHH=4 Hz,
CH), 2.00 (d,2JHH=8 Hz, CH), 1.69 (d,2JHH=8 Hz, CH), 1.03 (s, 3H, CH3), 0.88 (s,
3H, CH3), 0.73 (s, 3H, CH3). 13C NMR (100 MHz, DMSO-d6) d: 193.76 (C=O),
156.23, 153.14, 135.02, 134.31, 132.25, 131.66, 130.79, 130.18, 127.77, 126.26,
120.94, 114.82 (CN), 62.70 (C3), 49.80 (CH2), 42.10 (CH2), 38.42 (CH), 34.51
(CMe2), 32.02 (CH3), 29.63 (CH3), 21.11 (CH3). Anal. calcd. for C25H25N3O: C,
78.30; H, 6.57; N, 10.96 %. Found: C, 78.08; H, 6.45; N, 10.83 %.
2-amino-4-(4-bromophenyl)-7,7-dimethyl-5-oxo-1-phenyl-1,4,5,6,7,8-
hexahydroquinoline-3-carbonitrile (4f)
White crystals; IR (KBr, mmax,cm-1): 3,456, 3,328 (NH2), 2,160 (CN), 1,648 (C=O),
1
1,587 (C=C). H NMR (400 MHz, DMSO-d6) d: 7.63–7.23 (m, 9H, CH–Ar), 5.71
(s, 2H, NH2), 4.46 (s, 1H, CH), 2.21 (d, 2JHH=4 Hz, CH), 2.17 (d, 2JHH=4 Hz, CH),
2
2.01 (d, JHH=8 Hz, CH), 1.70 (d,2JHH=8 Hz, CH), 0.88 (s, 3H, CH3), 0.73 (s, 3H,
CH3). 13C NMR (100 MHz, DMSO-d6) d: 192.25 (C=O), 157.14, 154.66, 135.29,
133.27, 132.92, 131.62, 131.43, 128.36, 126.03, 122.88, 120.95, 114.95 (CN), 61.69
(C3), 49.75 (CH2), 43.22 (CH2), 38.58 (CH), 35.90 (CMe2), 31.69 (CH3), 29.50
(CH3). Anal. calcd. for C24H22BrN3O: C, 64.29; H, 4.95; N, 9.37 %. Found: C,
64.07; H, 4.78; N, 9.19 %.
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